Contents

Extension of the C17α alkyl chain longer than an ethyl group abolishes androgenic activity and converts the drug into an antiandrogen, as in topterone (17α-propyltestosterone) and allylestrenol (17α-allyl-3-deketo-19-nortestosterone) (an extended-chain variant of ethylestrenol). Conversely, replacement of the C17α alkyl group with an ethynyl group greatly reduces but does not abolish androgenic activity, as in ethisterone (17α-ethynyltestosterone) and norethisterone (17α-ethynyl-19-nortestosterone).[1] Similarly to extension of the C17α alkyl chain, extension of the C17α ethynyl chain abolishes androgenic activity, as with dimethisterone (6α,21-dimethylethisterone). Dienogest, which is antiandrogenic, features extension of the C17α chain in the form of a cyanomethyl group at the C17α position.

1.
Organic compound
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An organic compound is virtually any chemical compound that contains carbon, although a consensus definition remains elusive and likely arbitrary. Organic compounds are rare terrestrially, but of importance because all known life is based on organic compounds. The most basic petrochemicals are considered the building blocks of organic chemistry, for historical reasons discussed below, a few types of carbon-containing compounds, such as carbides, carbonates, simple oxides of carbon, and cyanides are considered inorganic. The distinction between organic and inorganic compounds, while useful in organizing the vast subject of chemistry. Organic chemistry is the science concerned with all aspects of organic compounds, Organic synthesis is the methodology of their preparation. The word organic is historical, dating to the 1st century, for many centuries, Western alchemists believed in vitalism. This is the theory that certain compounds could be synthesized only from their classical elements—earth, water, air, vitalism taught that these organic compounds were fundamentally different from the inorganic compounds that could be obtained from the elements by chemical manipulation. Vitalism survived for a while even after the rise of modern atomic theory and it first came under question in 1824, when Friedrich Wöhler synthesized oxalic acid, a compound known to occur only in living organisms, from cyanogen. A more decisive experiment was Wöhlers 1828 synthesis of urea from the inorganic salts potassium cyanate, urea had long been considered an organic compound, as it was known to occur only in the urine of living organisms. Wöhlers experiments were followed by others, in which increasingly complex organic substances were produced from inorganic ones without the involvement of any living organism. Even though vitalism has been discredited, scientific nomenclature retains the distinction between organic and inorganic compounds, still, even the broadest definition requires excluding alloys that contain carbon, including steel. The C-H definition excludes compounds that are considered organic, neither urea nor oxalic acid is organic by this definition, yet they were two key compounds in the vitalism debate. The IUPAC Blue Book on organic nomenclature specifically mentions urea and oxalic acid, other compounds lacking C-H bonds but traditionally considered organic include benzenehexol, mesoxalic acid, and carbon tetrachloride. Mellitic acid, which contains no C-H bonds, is considered an organic substance in Martian soil. The C-H bond-only rule also leads to somewhat arbitrary divisions in sets of carbon-fluorine compounds, for example, CF4 would be considered by this rule to be inorganic, whereas CF3H would be organic. Organic compounds may be classified in a variety of ways, one major distinction is between natural and synthetic compounds. Another distinction, based on the size of organic compounds, distinguishes between small molecules and polymers, natural compounds refer to those that are produced by plants or animals. Many of these are extracted from natural sources because they would be more expensive to produce artificially

2.
Alkyl
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In organic chemistry, an alkyl substituent is an alkane missing one hydrogen. The term alkyl is intentionally unspecific to include many possible substitutions, an acyclic alkyl has the general formula CnH2n+1. A cycloalkyl is derived from a cycloalkane by removal of an atom from a ring and has the general formula CnH2n-1. Typically an alkyl is a part of a larger molecule, in structural formula, the symbol R is used to designate a generic alkyl group. The smallest alkyl group is methyl, with the formula CH3−, the word root alkyl is encountered in several contexts. Alkylation is an important operation in refineries, for example in the production of high-octane gasoline, alkylating antineoplastic agents refer to a class of compounds that are used to treat cancer. In such case, the alkyl is used loosely. For example, nitrogen mustards are well-known alkylating agents, but they are more complex than a mere hydrocarbon, in chemistry, alkyl refers to a group, a substituent, that is attached to other molecular fragments. For example, alkyl lithium reagents have the empirical formula Li, a dialkyl ether is an ether with two alkyl groups, e. g. diethyl ether. In medicinal chemistry, the incorporation of alkyl chains into some chemical compounds increases their lipophilicity and this strategy has been used to increase the antimicrobial activity of flavanones and chalcones. Usually alkyl groups are attached to atoms or groups of atoms. Free alkyls occur as neutral compounds, as anions, or as cations, the neutral alkyl free radicals have no special name. Such species are encountered only as transient intermediates, but some are quite stable. Typically alkyl cations are generated using super acids, alkyl anions are observed in the presence of strong bases, alkyls are commonly observed in mass spectrometry of organic compounds. The simplest series have the general formula CnH2n+1, alkyls include methyl, CH3·, ethyl, propyl, butyl, pentyl, and so on. Alkyl groups that one ring have the formula CnH2n−1, e. g. cyclopropyl and cyclohexyl. First, five atoms comprise the longest straight chain of carbon centers, the parent five-carbon compound is named pentane. The methyl substituent or group is highlighted red, according to the usual rules of nomenclature, alkyl groups are included in the name of the molecule before the root, as in methylpentane

3.
Methyl group
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A methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms — CH3. In formulas, the group is often abbreviated Me, such hydrocarbon groups occur in many organic compounds. It is a stable group in most molecules. While the methyl group is part of a larger molecule. The anion has eight electrons, the radical seven and the cation six. All three forms are highly reactive and rarely observed, the methylium cation exists in the gas phase, but is otherwise not encountered. Some compounds are considered to be sources of the CH3+ cation, the methanide anion exists only in rarefied gas phase or under exotic conditions. It can be produced by electrical discharge in ketene at low pressure, such reagents are generally prepared from the methyl halides, M + CH3X → MCH3 where M is an alkali metal. The methyl radical has the formula CH3 and it exists in dilute gases, but in more concentrated form it readily dimerizes to ethane. It can be produced by decomposition of only certain compounds. The reactivity of a methyl group depends on the adjacent substituents, methyl groups can be quite unreactive. For example, in compounds, the methyl group resists attack by even the strongest acids. The oxidation of a group occurs widely in nature and industry. The oxidation products derived from methyl are CH2OH, CHO, for example, permanganate often converts a methyl group to a carboxyl group, e. g. the conversion of toluene to benzoic acid. Ultimately oxidation of methyl groups gives protons and carbon dioxide, as seen in combustion, demethylation is a common process, and reagents that undergo this reaction are called methylating agents. Common methylating agents are dimethyl sulfate, methyl iodide, and methyl triflate, methanogenesis, the source of natural gas, arises via a demethylation reaction. Certain methyl groups can be deprotonated, for example, the acidity of the methyl groups in acetone is about 1020 more acidic than methane. The resulting carbanions are key intermediates in many reactions in organic synthesis and biosynthesis, fatty acids are produced in this way

4.
Ethyl group
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In chemistry, an ethyl group is an alkyl substituent derived from ethane. It has the formula –CH2CH3 and is often abbreviated Et. Ethylation is the formation of a compound by introduction of the ethyl group, the most widely practiced example of this reaction is the ethylation of benzene. Approximately 24.7 million tons were produced in 1999, ethylbenzene is the precursor to styrene, the precursor to polystyrene. Many ethyl-containing compounds are generated by electrophilic ethylation, i. e. treatment of nucleophiles with sources of Et+, triethyloxonium tetrafluoroborate BF4 is such a reagent. For good nucleophiles, less electrophilic reagents are employed, such as ethyl halides, in unsymmetrical ethylated compounds, the methylene protons in the ethyl substituent are diastereotopic. Chiral reagents are known to modify such substituents. The name of the group is derived from the Aether, the first-born Greek elemental god of air and hyle, the name ethyl was coined in 1835 by the Swedish chemist Jöns Jacob Berzelius

5.
Intramuscular injection
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Intramuscular injection is the injection of a substance directly into a muscle. In medicine, it is one of alternative methods for the administration of medications. Muscles have larger and more vessels than subcutaneous tissue and injections here usually have faster rates of absorption than subcutaneous injections or intradermal injections. Depending on the site, an administration is limited to between 2 and 5 milliliters of fluid. Platelet-rich plasma injections can be administered intramuscularly, certain substances are injected intramuscularly for recreational purposes. Possible sites for IM injection include, deltoid, dorsogluteal, rectus femoris, vastus lateralis, sites that are bruised, tender, red, swollen, inflamed or scarred are avoided. The deltoid muscle site is recommended for use with injections of small volume, usually equal or less than 1 ml and this site is not recommended for repeated injections, due to its small area, it is difficult to rotate the injection site. To locate the site, palpate the lower edge of the acromion process, inject in the upside down triangle that forms with its base at the acromion process and its midpoint in line with the axilla. The ventrogluteal site is recommended for injections requiring a larger volume to be administered, greater than 1 ml and it is also given for narcotic, antibiotic, sedative and anti-emetic medications. To locate the site, place the palm of your hand over the greater trochanter. The right hand is used for the hip and left hand is used for the right hip. Place the index finger on the superior iliac spine and run the middle finger back along the iliac crest. The injection is given in the center of the triangle that is formed, the vastus lateralis site is the recommended site for infants less than 7 months old and those unable to walk, with loss of muscular tone. To locate the site, divide the front thigh into thirds vertically and horizontally to make nine squares and inject in the outer middle square. Use of this site is associated with skin and tissue trauma, muscle fibrosis and contracture, haematoma, nerve palsy and paralysis, as well as infectious processes such as abscess and gangrene. The injection site is located by dividing the buttock into four with a plus shaped cross, the selected site is cleansed with an antimicrobial and is allowed to dry. It is injected with the dominant hand using a quick, darting motion perpendicular to the body at an angle between 72 and 90 degrees, as a faster injection is less painful. The needle is then stabilized with the nondominant hand while the dominant hand slides to the plunger to slowly instill the medication, the CDC does not recommend the outdated practice of aspirating for blood to rule out injecting into a blood vessel

6.
Estrogen
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Estrogen or oestrogen is the primary female sex hormone as well as a medication. It is responsible for the development and regulation of the reproductive system. Estrogen may also refer to any substance, natural or synthetic, the estrane steroid estradiol is the most potent and prevalent endogenous estrogen, although several metabolites of estradiol also have estrogenic hormonal activity. They are one of three types of sex hormones, the others being androgens/anabolic steroids like testosterone and progestogens like progesterone, estrogens are synthesized in all vertebrates as well as some insects. Their presence in both vertebrates and insects suggests that sex hormones have an ancient evolutionary history. The three major naturally occurring forms of estrogen in women are estrone, estradiol, and estriol, another type of estrogen called estetrol is produced only during pregnancy. Quantitatively, estrogens circulate at lower levels than androgens in both men and women, while estrogen levels are significantly lower in males compared to females, estrogens nevertheless also have important physiological roles in males. Like all steroid hormones, estrogens readily diffuse across the cell membrane, once inside the cell, they bind to and activate estrogen receptors which in turn modulate the expression of many genes. Additionally, estrogens bind to and activate rapid-signaling membrane estrogen receptors, the three major naturally occurring estrogens in women are estrone, estradiol, and estriol. Estradiol is the predominant estrogen during reproductive years both in terms of serum levels as well as in terms of estrogenic activity. During menopause, estrone is the predominant circulating estrogen and during pregnancy estriol is the predominant circulating estrogen in terms of serum levels. Though estriol is the most plentiful of the three estrogens it is also the weakest, whereas estradiol is the strongest with a potency of approximately 80 times that of estriol. Thus, estradiol is the most important estrogen in non-pregnant females who are between the menarche and menopause stages of life, however, during pregnancy this role shifts to estriol, and in postmenopausal women estrone becomes the primary form of estrogen in the body. Another type of estrogen called estetrol is produced only during pregnancy, all of the different forms of estrogen are synthesized from androgens, specifically testosterone and androstenedione, by the enzyme aromatase. Estradiol, estrone, and estriol have all been approved as drugs and are used medically. Estetrol is currently under development for medical indications, but has not yet approved in any country. A variety of synthetic estrogen esters, such as estradiol valerate, estradiol cypionate, estradiol acetate, estradiol undecylate, polyestradiol phosphate, the aforementioned compounds behave as prodrugs to estradiol, and are longer-lasting in comparison. Esters of estrone and estriol also exist and are employed in clinical medicine, ethinylestradiol is a more potent synthetic analogue of estradiol that is used widely in hormonal contraceptives

7.
Dihydrotestosterone
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Dihydrotestosterone, or 5α-dihydrotestosterone, also known as 5α-androstan-17β-ol-3-one, is an endogenous androgen sex steroid and hormone. The enzyme 5α-reductase catalyzes the formation of DHT from testosterone in certain tissues including the prostate gland, seminal vesicles, epididymides, skin, hair follicles, liver and this enzyme mediates reduction of the C4-5 double bond of testosterone. Relative to testosterone, DHT is considerably more potent as an agonist of the androgen receptor. DHT has an affinity of 0.25 to 0.5 nM for the human AR, the dissociation rate of DHT from the AR is 5-fold slower than that of testosterone. The EC50 of DHT for activation of the AR is 0.13 nM, in bioassays, DHT has been found to be 2. 5- to 10-fold more potent than testosterone. The terminal half-life of DHT in the body is longer than that of testosterone, a study of transdermal DHT and testosterone treatment reported terminal half-lives of 2.83 hours and 1.29 hours, respectively. An example illustrating the significance of DHT for the development of sex characteristics is congenital 5α-reductase type II deficiency. This genetic mutation can result in pseudohermaphroditism, the condition typically presents with underdeveloped male genitalia and prostate. Males with this condition are often raised as girls due to their lack of male genitalia. At the onset of puberty, although their DHT levels remain very low and their musculature develops like that of other male adults. After puberty, men with this condition have a deficiency of pubic and body hair. They also reportedly have no incidence of prostate cancer, unlike other androgens such as testosterone, DHT cannot be converted by the enzyme aromatase into an estrogen like estradiol. In the case of female androgenic alopecia, on the hand, the situation is more complex. Women with increased levels of DHT may develop symptoms of such as certain androgynous masculine secondary sex characteristics, including a deepened voice. In men, prostate growth and differentiation are highly dependent on androgens, especially DHT, both finasteride and dutasteride are approved for the treatment of BPH and androgenic alopecia. Dutasteride is three times more potent than finasteride in inhibiting the type II enzyme and 100 times more potent than finasteride in inhibiting the type I form of the DHT-producing enzyme, both finasteride and dutasteride are potent inhibitors of the third isotype of the enzyme. Acne, hirsutism, and seborrhea are also DHT-related conditions, in addition, antiandrogens like cyproterone acetate, spironolactone, and bicalutamide, as well as estrogens like ethinylestradiol, may also be used to treat these conditions. DHT is synthesized from testosterone by the enzyme 5α-reductase, in males, approximately 5% of testosterone undergoes 5α-reduction into DHT

8.
Nandrolone
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Nandrolone, also known as 19-nortestosterone or 19-norandrostenolone, is a synthetic anabolic-androgenic steroid derived from testosterone. The drug itself is inactive due to its lack of a 17α-alkyl group and is not actually employed in medicine. The positive effects of the drug include muscle growth, appetite stimulation and increased red cell production. Clinical studies have shown it to be effective in treating anemia, osteoporosis and some forms of neoplasia including breast cancer, the lack of alkylation on the 17α-carbon drastically reduces the hepatotoxic potential of nandrolone. Erectile dysfunction is attributed to the action of DHN in the penis since dihydrotestosterone is a known sexual modulator. In addition to its activity, unlike many other AAS. It binds to the receptor with approximately 22% of the affinity of progesterone. The progestogenic activity of nandrolone may serve to augment its antigonadotropic effects, Nandrolone has a very high ratio of anabolic to androgenic action. In fact, nandrolone-like AAS like nandrolone itself and trenbolone are said to have among the highest ratio of anabolic to androgenic effect of all AAS. This is attributed to the fact that, whereas testosterone is potentiated via conversion into dihydrotestosterone in androgenic tissues, Nandrolone is metabolized by the enzyme 5α-reductase, among others. Metabolites of nandrolone include 5α-dihydronandrolone, 19-norandrosterone, and 19-noretiocholanolone, Nandrolone is also known chemically as estra-4-en-17β-ol-3-one or 19-norandrost-4-en-17β-ol-3-one. It is the 19-demethylated analogue of testosterone, and for reason, is also known as 19-nortestosterone. A large number of nandrolone esters have been marketed and used clinically, the most commonly used esters are nandrolone decanoate and nandrolone phenylpropionate. Nandrolone is the parent compound of a group of AAS. Notable examples include the non-17α-alkylated trenbolone and the 17α-alkylated ethylestrenol and metribolone, Nandrolone is also the parent compound of a large group of progestins. They are subdivided into two groups, the estranes and the gonanes, initial reaction constituents of 1, 4-dimetalation of the most electron deficient positions of the aromatic ring–in the case of an estrogen, the 1 and 4-positions. Treatment of this product with weak acid, oxalic acid for e. g. leads to the hydrolysis of the ether, producing β. Hydrolysis under more sternuous conditions results in migration/conjugation of the olefin to yield nandrolone, treatment of 4 with decanoic anhydride and pyridine affords nandrolone decanoate

9.
Methyltestosterone
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Testosterone is a medication and naturally occurring steroid hormone. It is an androgen and anabolic steroid and is used to treat male hypogonadism and it may also be used to increase athletic ability in the form of doping. It is unclear if the use of testosterone for low levels due to aging is beneficial or harmful. Testosterone can be used as a gel or patch that is applied to the skin, injection into a muscle, tablet that is placed in the cheek, common side effects from testosterone medication include acne, swelling, and breast enlargement in males. Serious side effects may include liver toxicity, heart disease, women and children who are exposed may develop virilization. It is recommended that individuals with prostate cancer not use the medication and it can cause harm to the baby if used during pregnancy or breastfeeding. Testosterone was first isolated in 1935, rates of use have increased three times in the United States between 2001 and 2011. It is on the World Health Organizations List of Essential Medicines and it is available as a generic medication. The price depends on the dose and form of the product, the primary use of testosterone is the treatment of males with too little or no natural testosterone production, also termed hypogonadism or hypoandrogenism. This treatment is referred to as hormone replacement therapy, or alternatively and it is used to maintain serum testosterone levels in the normal male range. Decline of testosterone production with age has led to interest in testosterone supplementation, Testosterone deficiency is an abnormally low testosterone production. It may occur because of testicular dysfunction or hypothalamic-pituitary dysfunction and may be congenital or acquired, Testosterone levels may decline gradually with age. The United States Food and Drug Administration stated in 2015 that neither the nor the safety of testosterone supplement have been established for low testosterone levels due to aging. The FDA has required that labels on testosterone include warnings about increased risk of heart attacks, Testosterone supplementation is effective in the short term for hypoactive sexual desire disorder. However, its long term safety is unclear, treating low androgen levels with testosterone is not generally recommended in women when it is due to hypopituitarism, adrenal insufficiency, or following surgical removal of the ovaries. It is also not usually recommended for improving cognition, the risk of heart disease, Testosterone is used as a form of doping among athletes in order to improve performance. Testosterone is classified as an agent and is on the World Anti-Doping Agency List of Prohibited Substances. Anabolic-androgenic steroids, including testosterone and its esters, have also taken to enhance muscle development, strength

10.
Ethisterone
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It was the second progestogen to be marketed and was both the first orally active progestogen and the first progestin to be introduced. Although ethisterone has largely superseded by newer drugs and is now little used. Moreover, the 19-nortestosterone progestins, such as norethisterone, are derived from ethisterone and are used as hormonal contraceptives. Ethisterone is described as a weak progestogen, similarly to its analogue dimethisterone. As such, there is a separation in the ratios of androgenic and progestogenic activity for ethisterone and norethisterone. Due to its activity, ethisterone has been associated with the masculinization of female fetuses in women who have taken it during pregnancy. As such, ethisterone does not appear to share the activity of norethisterone. Ethisterone was synthesized in 1938 by Hans Herloff Inhoffen, Willy Logemann, Walter Hohlweg, however, the androgenic activity of ethisterone was attenuated and it showed considerable progestogenic activity. As such, it was developed as a progestogen instead and was marketed in Germany in 1939 as Proluton C and by Schering in the U. S. in 1945 as Pranone, among other brand names. 19-Norprogesterone 17α-Methylprogesterone List of steroidal progestogens List of androgens/anabolic steroids Inhoffen HH, Logemann W, Hohlweg W, Schering Proluton C tablets c.1939 Quinkert G. Hans Herloff Inhoffen in His Times, hoboken NJ, John Wiley & Sons

11.
Dimethisterone
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Dimethisterone, also known as 6α, 21-dimethylethisterone, is a steroidal progestin related to ethisterone. Dimethisterone was derived from modification of ethisterone via introduction of methyl groups at the C6α and C21 positions. Relative to ethisterone, it is 12 times as potent orally as a progestogen in animals, however, in spite of its improved potency over ethisterone, it is a weak progestogen relative to most other progestins, in fact one of the weakest known. Dimethisterone was introduced in the United States as a contraceptive in combination with high doses of ethinylestradiol under the brand name Oracon in 1965. The improved potency of dimethisterone due to 6α-methylation reportedly served as the basis for the synthesis of medroxyprogesterone acetate, whereas hydroxyprogesterone acetate is around twice as potent as ethisterone orally, medroxyprogesterone acetate shows 10 to 25 times the potency of ethisterone

12.
Dienogest
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Dienogest is a progestin, or a synthetic progestogen, of the 19-nortestosterone group. It is available in combination with estradiol valerate or ethinylestradiol for use as a contraceptive, and by itself for the treatment of endometriosis in Europe, Australia. Although available in combination with estrogen as a contraceptive in the United States, in addition to its progestogenic effects, dienogest has antiandrogenic activity, and as a result can improve androgenic symptoms such as acne. It is a non-ethynylated progestin which is related to testosterone. Dienogest is used primarily as a contraceptive in combination with ethinylestradiol and it is given as a tablet containing 2 mg of dienogest and 30 μg of ethinylestradiol. Dienogest is also available in an oral contraceptive pill combined with estradiol valerate, marketed as Natazia in the United States and Qlaira in some European countries. This formulation is approved for the treatment of heavy menstrual bleeding. Dienogest is also approved in Europe, Australia, Malaysia, Singapore and it has been shown to be equally effective as leuprorelin, which is a second line medication against endometriosis. Adverse effects associated with dienogest are the same as expected of a progestogen. These include weight gain, increased pressure, breast tenderness. It produces no androgenic side effects and has little effect on metabolic, dienogest has relatively low affinity for the progesterone receptor in vitro in human uterus tissue, about 10% that of progesterone. In spite of its relatively weak affinity for the PR, the shows strong progestogenic effects on the endometrium. Dienogest is said to be one of the only 19-nortestosterone derivative progestins that does not have androgenic properties, in fact, it actually has antiandrogen activity, about 30–40% of that of cyproterone acetate, and can improve androgenic symptoms such as acne and hirsutism. The drug does not interact with the estrogen, glucocorticoid, or mineralocorticoid receptor, however, it has limited impact on Gonadotropin Releasing Hormone, and thus does not lower LH significantly compared to other progestins. Metabolites of dienogest, such as 9α, 10β-dihydrodienogest and 3, 5α-tetrahydrodienogest, show greater affinity for the PR, the minimum effective dose of oral dienogest required to inhibit ovulation is 1 mg/day. The inhibition of ovulation by dienogest reportedly occurs mainly via peripheral action as opposed to central action on gonadotropin secretion, dienogest is rapidly absorbed and has high bioavailability of approximately 90%. It is exclusively protein-bound to albumin, and does not bind to sex hormone-binding globulin or corticosteroid-binding globulin, the drug is metabolized in the liver mainly by CYP3A4. Its metabolites are said to be inactive and to be rapidly excreted, the terminal half-life of dienogest is 10 hours

13.
Chlorodehydromethyltestosterone
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It is the 4-chloro-substituted derivative of metandienone. CDMT was the first original product of Jenapharm, an East German pharmaceutical company, the patent registration took place in 1961. The idea of combining the structures of 4-chlorotestosterone and metandienone originated from the chemist Albert Stachowiak, at the time this represented a unique dissociation of anabolic and androgenic effects after oral administration. The product had been introduced for use in 1965. CDMT was the key steroid administered to approximately 10,000 athletes from East Germany as secret official policy, the doping program was run by the East German Government from about 1968 until 1989 when the Berlin wall was destroyed. The doping program was known as STASI14.25, after the collapse of the East German regime, people responsible for the forced doping were found guilty of causing grievous bodily harm to about 10,000 sportspeople, victims were compensated. In later life former athletes developed serious health problems believed due to the drugs, following allegations by the German documentary of widespread doping the IOC kicked off a reanalysis of Beijing 2008 and London 2012 samples. Weightlifters in particular were found to have used Dehydrochlormethyltestosterone – Most of the doped athletes coming from Russia, Ukraine, however, the method developed by Dr Grigory Rodchenkov in 2011 was used in 2016 to detect long-term metabolites of Oral Turinabol while retesting the athletes Olympic samples

14.
Metandienone
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Metandienone was originally developed in 1957 by CIBA and marketed in Germany and the United States. It is currently a controlled substance in the U. S. and UK, metandienone is readily available without a prescription in certain countries such as Mexico, and is also manufactured in Asia and many Eastern European countries. Metandienone was first synthesized in 1956 by researchers at the CIBA laboratories in Basel, CIBA filed for a US patent in 1957, and began marketing the compound as Dianabol in 1958. Beginning soon afterwards in 1959, CIBA collaborated with John Bosley Ziegler to test the effects of Dianabol on professional weightlifters. Ziegler had a relationship with Bob Hoffman, owner of York Barbell Company and coach of the US Olympic weightlifting team. The first tentative experiments were disappointing, for example, AAU Mr. America winner Jim Park reported that its only effect was to give him an instant erection upon seeing any female. However, Ziegler believed that Dianabol had significant potential as an anabolic, during the lead-up to the 1960 Olympics, he proposed to Hoffman that it be administered to top members of the American Olympic team. Hoffman, however, was cautious and later remarked it was too close to give to the men who represent the USA. According to Grimek, apparently, he doesn’t think it will do much good. Instead, Dianabol was given to lower level lifters to investigate its effectiveness. Among the first subjects were John Grimek, Bill March, Charles Vinci, Riecke gained muscle mass and strength rapidly, and reported a constant feeling of euphoria and energy. His results drew enormous interest among other elite weightlifters, and rumors spread that Ziegler had made a breakthrough in his research. He attempted to deflect their curiosity with hints of new isometric and hypnotic techniques, over the course of the next 2 years, Zieglers work with Riecke further explored the new drugs physical and psychological effects. Rieckes performance and mood consistently improved while taking Dianabol, and dramatically declined when he did not take it. John Fair also suggests that Riecke was among the first cases of steroid dependency, at one point mentioning the four times in letter. American football players and coaches were particularly interested in the new anabolic, early adopters included players for Oklahoma University and San Diego Chargers head coach Sid Gillman, who administered Dianabol to his team starting in 1963. In 1965, the FDA pressured CIBA to further document its legitimate medical uses, after CIBAs patent exclusivity period lapsed, other manufacturers began to market generic metandienone in the US. Following further FDA pressure, CIBA withdrew Dianabol in 1983, generic production shut down two years later, when the FDA revoked metandienones approval entirely in 1985

15.
Furazabol
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Furazabol, also known as androfurazanol, is an analogue of the anabolic steroid stanozolol. It differs from stanozolol by having a ring system in place of the pyrazole. It has a methyl group, which allows it to be taken orally. According to William Llewellyn, author of Anabolics 2007, the effects of furazabol are a myth. In the 1970s, research showed that furazabol along with many other orally-active AAS like Anavar lowered total serum cholesterol. It was subsequently established that the reduction from oral AAS was the result of suppressed HDL levels. The Canadian sprinter Ben Johnson tested positive for stanozolol after winning the medal in the 100 meter sprint at the 1988 Summer Olympics. His doctor, Jamie Astaphan, maintains that his sample was sabotaged because Johnson was administered furazabol. Subsequently, training partner and fellow Charlie Francis athlete Angela Issajenko and she substantiated this by stating that her supply of what she thought was furazabol was retested following the Dubin Inquiry and was found to be stanozolol, explaining the positive test

16.
Mestanolone
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Mestanolone is the 17α-methylated version of dihydrotestosterone. The systematic name of mestanolone is, 17β-hydroxy-17α-methylandrost-3-one and it is an orally bioavailable androgenic steroid that is highly androgenic while only slightly anabolic. It is incapable of aromatization and is not an agonist of the progesterone receptor, dosage Information Dosages range from 10 mg to 30 mg a day for males. Women should avoid Mestanolone for it is very androgenic, long-term use, more than 12 weeks, should be avoided do to hepatoxicity. Since Mestanolone is unable to convert to estrogen, it is useful during cutting phases or when one wishes to avoid excess weight gain. Synonyms Mestanolone is also known as methylandrostanolone or 17alpha-methylandrostanolone

17.
Oxymetholone
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Oxymetholone is a synthetic, orally active anabolic-androgenic steroid and 17α-methylated derivative of dihydrotestosterone that is marketed in the United States, Europe, and elsewhere in the world. It was first described in a 1959 paper by scientists from Syntex and its primary clinical applications include treatment of osteoporosis and anaemia, as well as stimulating muscle growth in malnourished or underdeveloped patients. The drug was approved for use by the FDA. Later, non-steroidal drugs such as epoetin alfa were developed and proven to be effective as a treatment for anaemia. The drug remained available despite this and eventually found a new use in treating HIV wasting syndrome, presented most commonly as a 50 mg tablet, oxymetholone is one of the strongest androgenic steroids available. Similarly, there is a risk of side effects, despite very low binding affinity with the androgen receptor, oxymetholone is highly effective in promoting extensive gains in body mass, mostly by greatly improving protein synthesis. For this reason, it is used by bodybuilders and athletes. In women, side effects include acne, changes in menstrual periods, deepened voice, hair growth on the chin or chest, male pattern baldness, enlarged clitoris. Because of its 17α-alkylated structure, oxymetholone is highly hepatotoxic, oxymetholone is also known by the chemical names 2-hydroxymethylene-17α-methyl-4, 5α-dihydrotestosterone and 2-hydroxymethylene-17α-methylandrostan-17β-ol-3-one

18.
Stanozolol
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Stanozolol, commonly sold under the name Winstrol and Winstrol Depot, is a synthetic anabolic steroid derived from dihydrotestosterone. It was developed by American pharmaceutical company Winthrop Laboratories in 1962, unlike most injectable anabolic steroids, stanozolol is not esterified and is sold as an aqueous suspension, or in oral tablet form. The drug has an oral bioavailability, due to a C17 α-alkylation which allows the hormone to survive first-pass liver metabolism when ingested. It is because of this that stanozolol is also sold in tablet form, Stanozolol has been used in both animal and human patients for a number of conditions. In humans, it has demonstrated to be successful in treating anaemia. Veterinarians may prescribe the drug to improve growth, red blood cell production, increase bone density. Additionally, stanozolol has been used in US horse racing, Stanozolol is subject to non-medically supervised off-label use by some athletes for its anabolic properties frequently presenting with concomitant reduction of body fat. Stanozolol is a derivative of dihydrotestosterone and thus not aromatized to oestrogens via the aromatase class of enzymes. Stanozolol is used by athletes and bodybuilders to lose fat while retaining lean body mass, Stanozolol is subject to extensive hepatic biotransformation by a variety of enzymatic pathways. The primary metabolites are unique to stanozolol and are detectable in the urine for up to 10 days after a single 5–10 mg oral dose, methods for detection in urine specimens usually involve gas chromatography-mass spectrometry or liquid chromatography-mass spectrometry. In 1962, Stanozolol was brought to market in the US by Winthrop under the tradename Winstrol, the FDA implemented its Drug Efficacy Study Implementation program to study and regulate drugs, including stanozolol, that had been introduced prior to the amendment. The DESI program was intended to classify all pre-1962 drugs that were already on the market as effective, ineffective, the FDA enlisted the National Research Council of the National Academy of Sciences to evaluate publications on relevant drugs under the DESI program. In June 1970 the FDA announced its conclusions on the effectiveness of certain anabolic steroid drugs, including stanozolol, anabolic steroids are without value as primary therapy but may be of value as adjunctive therapy. Equal or greater consideration should be given to diet, calcium balance, physiotherapy, and gave Sterling a timeline to submit further data for other indications it wanted for the drug. Sterling submitted data to the FDA intended to support the effectiveness of Winstrol for postmenopausal osteoporosis and aplastic anemia in December,1980, the FDAs Endocrinologic and Metabolic Drugs Advisory Committee considered the data submitted for osteoporosis in two meetings held 1981 and the data for aplastic anemia in 1983. In 1988, Sterling was acquired by Eastman Kodak for $5.1 billion, Sanofi had stanzolol manufactured in the US by Searle, which stopped making the drug in October 2002. Even with no drug in production, Sanofi sold the business to Ovation Pharmaceuticals in 2003. At that time, the drug had not been discontinued and was considered a treatment for hereditary angioedema and it is used as a performance-enhancing drug in race horses

19.
Desoxymethyltestosterone
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It was one of the first designer steroids to be marketed as a performance-enhancing drug to athletes and bodybuilders. Desoxymethyltestosterone is sometimes abbreviated as DMT, though it should not be confused with the hallucinogen dimethyltryptamine, desoxymethyltestosterone is unusual in that it is structurally a 2-ene compound, lacking the 3-keto group present in almost all commercial AAS. This does not mean it is a compound, and clinical research has determined that it is a fairly potent oral agent. Rat studies indicate that desoxymethyltestosterone has an anabolic effect 160% that of testosterone while being only 60% as androgenic, desoxymethyltestosterone was invented in 1961 by Max Huffman who obtained a patent on the compound the same year. It was described in the literature in 1963. However, it was never brought to market as a commercial drug, desoxymethyltestosterone was rediscovered by chemist, AAS enthusiast, and amateur bodybuilder Patrick Arnold in 2005. Arnold produced desoxymethyltestosterone and supplied it to Victor Conte of Bay Area Laboratory Co-operative, the substance had come under scrutiny after it was found to be present in several over-the-counter bodybuilding supplements

20.
Methasterone
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Methasterone, also known as methyldrostanolone, is an orally active anabolic-androgenic steroid that was never marketed through legitimate channels for medicinal purposes. It was brought to market, instead, in a fashion as a “designer steroid. ”Mebolazine is formed by hydrazone formation between 2 equivalents of methasterone with 1 equivalent of hydrazine. The synthesis of methasterone is first mentioned in the literature in 1956 in connection with research conducted by Syntex Corporation in order to discover a compound with anti-tumor properties, Methasterone was never a commercially available prescription drug. Its non-17α-alkylated counterpart, drostanolone, was commercialized by Syntex Corporation under the brand name Masteron, Methasterone resurfaced in 2005 as a “designer steroid”. It was brought to market by Designer Supplements as the ingredient of a dietary supplement named Superdrol. Its introduction into commerce may have represented an attempted circumvention of the U. S. Methasterone was therefore being sold as a dietary supplement. Don Catlin of the UCLA Olympic Laboratory, who conducted the studies, a warning by the FDA was issued soon after to the general public as well as to the distributor, Designer Supplements LLC, for the marketing of this compound. Methasterone was subsequently added to the World Anti-Doping Agency list of prohibited substances in sport, despite all of this, methasterone has resurfaced within the supplement industry on several occasions since its banning by WADA. Many cases of damage due to the use of methasterone have been cited in the medical literature

Nandrolone, also known as 19-nortestosterone, is an androgen and anabolic steroid (AAS) which is used in the form of …

QV Nandrolone Deca, a form of nandrolone used by athletes.

Nandrolone, with the differences from testosterone highlighted in red. The methyl group in testosterone at the C19 position has been removed, and the C17β position is where esters are attached to nandrolone.